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Brampton mayoral candidates, from left, John Sanderson, incumbent Susan Fennell, front-runner Linda Jeffrey and Devinder Sangha take part in a debate on young professionals’ issues at Lab-B, a collective of creative types and entrepreneurs, in the city’s downtown on Oct. 2. Ms. Fennell once ran for the federal Conservatives.J.P. MOCZULSKI/The Globe and Mail

The Liberal mayors across the GTA cheered on the surprise majority win of Kathleen Wynne's Grits this spring, and now Queen's Park is turning its eyes to Monday's municipal races in the region, when a red wave is expected to wash over the 905 area. If polls are to be trusted, Mississauga, Brampton, Vaughan, Markham and Oakville will all put Liberals into their mayors' offices.

At a time where transportation and infrastructure funding sit at the top of municipal agendas, the relationship between the Ontario Liberal majority government and mayors of its 905 cities is key to the prosperity of those municipalities in the next term of office – especially in Mississauga and Brampton. In these municipalities that have expanded rapidly in recent decades, infrastructure deficits are mounting. Funding, support and reinvigoration of these communities is vital to their success and, in turn, the prosperity of the province.

The possibility of former Liberal MPs Bonnie Crombie or Steve Mahoney being elected in Mississauga or former Liberal MPP Linda Jeffrey, who was in Ms. Wynne's cabinet, in Brampton "bodes well for good, strong relationships for both Mississauga and Brampton with the Wynne government," said Greg Sorbara, the province's former finance minister and an active Liberal party organizer. Liberals Frank Scarpitti in Markham, Maurizio Bevilacqua in Vaughan and Rob Burton in Oakville are also expected to be re-elected.

While Toronto mayoral front-runner John Tory was once leader of the province's Progressive Conservatives, insiders say he has nurtured a good relationship with Ms. Wynne. "There's a really close relationship between John Tory and Kathleen Wynne. And it's a good relationship, not the political banner, that's important," Mr. Sorbara said.

From transit projects, to new hospitals, to university funding, the work of municipal and provincial government is "very integrated," said Mississauga-Erindale Liberal MPP Harinder Takhar, who served as a cabinet minister in Dalton McGuinty's government. "You want to make sure we are all on the same wavelength and can actually do the things that are really important to our residents."

Sharing party stripes with the government of the day doesn't guarantee good municipal-provincial relations, but political watchers and Liberal insiders, including Mr. Sorbara, say it can open the door to better dialogue. As long-serving mayors in the region have shown, being able to communicate well with Queen's Park – whether through a cordial approach or a pugnacious one – is key.

After 36 years in office, Mississauga mayor Hazel McCallion established herself as elder stateswoman of municipal politics in the GTA, using her audacity to help Mississauga punch above its weight.

"The truth is she's the only person in the province that scares the bejesus out of me," former premier David Peterson once famously said of her.

While Ms. McCallion took a softer approach in her last few terms in office, she still maintained her "scrapper" persona when it worked in her favour, says Tom Urbaniak, who wrote a book about Mississauga's history and teaches political science at Cape Breton University. Ms. McCallion would attend meetings with provincial ministers and confront them aggressively, to the point of embarrassing them.

Neither Ms. Crombie nor Mr. Mahoney has a history of "making waves" or "carving out unique or exciting policy initiatives," Mr. Urbaniak said.

"Given their political track records, I suspect they will attempt a more low-key approach to relations with the senior levels of government than most of what we've seen for the political career of Hazel McCallion."

That said, earlier this month Ms. McCallion endorsed Ms. Crombie at a fundraiser, revealing she saw something unique in the candidate. "Bonnie is young and she's ambitious. She works hard. She's got some new ideas and I hope those new ideas will come forward," Ms. McCallion said.

Mr. Mahoney and Ms. Crombie both have ties to the Liberal party. Ms. Crombie has been an active member of the party since her youth, serving as president of the University of Toronto Liberals in her undergraduate days. From 2008 to 2011, Ms. Crombie was a Liberal MP. Having sat on the transportation and infrastructure standing committee, she said she knows who the players are on the federal level. Ms. Crombie said she is also in with Ms. Wynne. "I have great connections with the premier and the premier's office and the provincial level of government," she said.

Mr. Mahoney served as a Liberal MPP from 1987 to 1995 and stayed under the party banner in 1997 when he switched to federal politics, which included a brief stint as a minister in Jean Chrétien's cabinet. He said he still has a good rapport with the federal Liberals.

As for Queen's Park, he said, "My connections at the province go right up to the top and throughout every ministry."

Ms. Crombie has characterized Mr. Mahoney as "yesterday's man" – a candidate who had his time with all levels of government but whose relationships have gone stale. But Mr. Sorbara challenged that notion, saying if elected, Mr. Mahoney will have good relationships with Queen's Park "because he knows everyone there."

Mr. Takhar points out that Mr. Mahoney was appointed and reappointed by the current government as chair of the Workplace Safety and Insurance Board twice. Mr. Takhar sought the leadership of the Liberal party in 2013 and was backed in his bid by Ms. Crombie. He says Ms. Crombie and her opponent are so similar that it would be easy to work with either. But he endorsed Mr. Mahoney because "he has more current relationships than [Ms. Crombie] has and he has more endorsements from the MPPs."

At the end of the day, party affiliation isn't a dealbreaker, Mr. Takhar said. "It's more important if it's a person you can work with, if it's someone who is thinking about the same things you are."

That is where Brampton Mayor Susan Fennell, who is seeking re-election, stumbled, Mr. Sorbara says.

Though most of Ms. Fennell's career has been spent in local politics, in 1993 she ran in the federal election on the Progressive Conservative ticket. Mr. Sorbara described Ms. Fennell's relationship with the province as "much, much rockier" than Ms. McCallion's.

"She did not have a particularly strong ability to build effective relationships with the provincial government," he said.

Ms. Jeffrey, who represented the Brampton Centre and then Brampton-Springdale riding at Queen's Park and most recently served as Minister of Municipal Affairs, had a "terrible relationship" with Ms. Fennell, Mr. Sorbara said. Ms. Fennell's opponents have blamed perceived hostility between the two for a lack of major progress on a number of files, including transit.

The perception of Ms. Fennell as being strongly partisan was seen across departments, according to one former Liberal official. With Ms. McCallion, he said, "You always knew that what she was talking about was what Hazel thought rather than what would benefit her politically. Whereas that was not the sense really in Brampton."

While Ms. Jeffrey is known to be close to Ms. Wynne and served in her cabinet, her Liberal stripes don't mean that every project she has on her wish list will be funded by the province if she's elected, Mr. Sorbara said.

"They're not going to build a subway to Brampton because Linda's there. When Linda needs to make a case for something, she will know who to talk to and she'll know how the system works," Mr. Sorbara said. "When issues arise, because of the personal relationship, the quality of the dialogue will be better."

For that reason, it made more sense for Ms. McCallion, rather than Toronto Mayor Rob Ford – who has never had a warm relationship with the province – to steer the ship this past winter when GTA mayors united to request ice storm relief funds from Queen's Park. This united regional approach could become even more common if a slate of Liberal mayors is elected in the 905.

A former Liberal official told The Globe and Mail he anticipates more co-ordinated plays like that in the future, and a stronger political alignment would only help the cause.

"What was interesting on that was it was Mississauga-Hazel led. Obviously the region really needs that and it'll be interesting to see who takes up that role now," he said.